Exam 1 (Monday, July 6, 2015)

Chem 231 Summer 2015 Assigned Homework Problems Last updated: Friday, July 24, 2015 Problems Assigned from Essential Organic Chemistry, 2 nd Edition, Paula Yurkanis Bruice, Prentice Hall, New York, NY, 2010 Exam 1 (Monday, July 6, 2015) Chapter 1 How the Electrons in an Atom are Distributed 1.2 2, 3, 4, 5 Ionic and Covalent Bonds 1.3 6, 7, 8 How the Structure of a Compound is Represented 1.4 11, 12, 13, 14, 15, 16, 17, 18 How Single Bonds are Formed in Organic Compounds 1.7 How a Double Bond is Formed: The Bonds in Ethene 1.8 20 The Bonds in Water The Bonds in Ammonia and in the Ammonium Ion End of the Chapter Questions 31, 32, 34, 39, 40, 41, 42, 43, 50 Chapter 2 An Introduction to Acids and Bases 2.1 1, 2 pk a and ph 2.2 3, 4, 5, 6 Organic Acids and Bases 2.3 7, 8 How to Predict the Outcome of an Acid-Base Reaction 2.4 9 How to Determine the Position of Equilibrium 2.5 10 How the Structure of an Acid Affects its pk a 2.6 11, 12, 13, 14 Lewis Acids and Bases 2.9 19, 20 End of the Chapter Questions 21, 22, 23, 24, 28, 30, 34 Chapter 3 How Alkyl Substituents are Named 3.1 1, 2, 3, 4, 5 The Nomenclature of Alkanes 3.2 6, 8 The Nomenclature of Cycloalkanes Skeletal Structures 3.3 9, 10, 11, 12 The Nomenclature of Alkyl Halides 3.4 13, 14 The Classification of Alkyl Halides, Alcohols, and Amines 3.5 15, 16 End of the Chapter Questions 34, 35, 36, 41, 45, 54 Page 1 of 7

Exam 2 (Monday, July 13, 2015) Chapter 3 The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines 3.7 21, 22, 23, 25, 26, 27 Conformers of Cyclohexane 3.10 30 Conformers of Monosubstituted Cyclohexanes 3.11 31 Conformers of Disubstituted Cyclohexanes 3.12 32, 33 End of the Chapter Questions 38, 42, 44,46, 52, 56 Chapter 4 The Nomenclature of Alkenes 4.2 3, 4 Alkenes Can Have Cis-Trans Isomers 4.4 6 Nameing Alkenes using the E,Z - System 4.5 7, 8, 9, 10 Relative Stability of Alkenes 4.6 11, 12 How Alkenes React: Curved Arrows 4.7 13, 14, 15 End of the Chapter Questions 19, 21, 22, 23, 24, 26, 27, 28, 29, 30, 31, 33, 35, 39, 41 Chapter 5 The addition of a Hydrogen Halide to an Alkene 5.1 1 Carbocation Stability Depends on the Number of Alkyl Subsituents Attached to the Positively Charged 5.2 2, 3 Carbon Electrophilic Addition Reactions are Regioselective 5.3 4, 5 The Addition of Water to an Alkene 5.4 6 The Addition of an Alcohol to an Alkene 5.5 7, 8, 9, 10 Nomenclature of Alkynes 5.7 13, 14, 16 The Addition of a Hydrogen Halide to an Alkyne 5.10 18 The Addition of Water to an Alkyne 5.11 19, 20, 21 The Addition of Hydrogen to Alkenes and Alkynes 5.12 22, 23 Synthetic Polymers 5.16 29, 30, 31 Radicals in Biological Systems 5.17 End of the Chapter Questions 33, 34, 35, 36, 39, 40, 41, 45a, 49, 50, 51, 61, 64, 68, 69, 70 Page 2 of 7

Exam 3 (Monday, July 20, 2015) Chapter 6 Cis-trans Isomers Result from Restricted Rotation 6.1 1, 2 A Chiral Object has a non-superimposable Mirror Image 6.2 3 An Asymmetric Center is the Cause of Chirality in a Molecule 6.3 4, 5 Isomers with One Asymmetric Center 6.4 6 How to Draw Enantiomers 6.5 7, 8 Naming Enantiomers By the R,S System 6.6 9, 10, 11, 12, 13, 14 Isomers with More than One Asymmetric Center 6.9 20, 21, 22, 23 Meso Compounds Have Asymmetric Centers But Are Optically Inactive 6.10 24, 25 Receptors 6.12 26 Stereochemistry of Enzyme-Catalyzed Reactions 6.14 29 End of the Chapter Questions 30, 32, 33, 34, 35, 36, 38, 39, 42, 43, 45, 46, 47, 48, 50, 51, 52, 55 Chapter 7 Delocalized Electrons and Their Effect on Stability, Reactivity, and pka The Structure of Benzene 7.1 Benzene has Delocalized Electrons 7.2 Resonance Contributors and The Resonance Hybrid 7.3 How to Draw Resonance Contributors 7.4 1, 2 Predicted Stabilities of Resonance Contributors 7.5 3, 4 Examples that Illustrate How Delocalized Electrons Affect Stability 7.7 8, 10, 11 Examples that Illustrate How Delocalized Electrons can Affect the Product of a Reaction 7.8 12, 13, 14, 15 Examples that Illustrate How Delocalized Electrons Can Affect pka 7.9 17, 18, 19 End of the Chapter Questions 23, 24, 25, 26, 28, 30, 31, 33, 37, 38, 41, 46 Chapter 8 - Aromaticity Introduction The Two Criteria for Aromaticity 8.1 Applying the Criteria for Aromaticity 8.2 1, 2, 3, 4, 5 Aromatic Heterocyclic Compounds 8.3 6 Nomenclature of Monosubstituted Benzenes 8.4 8 How Benzene Reacts 8.5 End of the Chapter Questions 23, 25, 26 Page 3 of 7

Exam 4 (Monday, July 27, 2015) Chapter 8 - Aromaticity How Benzene Reacts 8.5 The General Mechanism for Electrophilic Aromatic Substitution Reactions 8.6 Halogenation of Benzene 8.7 Nitration of Benzene 8.8 Sulfonation of Benzene 8.9 Friedel-Crafts Acylation of Benzene 8.10 9 Friedel-Crafts Alkylation of Benzene 8.11 10, 11 How Some Substituents on a Benzene Ring can be Chemically Changed 8.12 12, 13 Nomenclature of Disubstituted Benzenes 8.13 14, 15, 16 The Effect of Substituents on Reactivity 8.14 17, 18 The Effect of Substituents on Orientation 8.15 19 End of the Chapter Questions 24, 28, 32 Chapter 9 Substitution and Elimination Reactions of Alkyl Halides How Alkyl Halides React 9.1 The Mechanism of an SN2 Reaction 9.2 2,3 Factors That Affect SN2 Reactions 9.3 4, 5, 6 The Mechanism of an SN1 Reaction 9.4 7, 8 Factors That Affect SN1 Reactions 9.5 9 Comparing the SN2 and SN1 Reactions of Alkyl Halides 9.6 10, 11, 12 Elimination Reactions of Alkyl Halides 9.7 13 Products of Elimination Reactions 9.8 14, 15, 16, 17 Biological Methylating Reagents 9.14 End of the Chapter Questions 30, 31, 32, 34, 37, 38, 39, 42, 44, 45, 49, 52, 53 Chapter 10 Reactions of Alcohols, Amines, Ethers, and Epoxides The Nomenclature of Alcohols 10.1 1, 2, 3 Substitution Reactions of Alcohols 10.2 4, 5, 6, 7 Elimination Reactions of Alcohols: Dehydration 10.3 10, 11 Oxidation of Alcohols 10.4 12, 13 Nucleophilic Substitution Reactions of Epoxides 10.8 18, 19 End of the Chapter Questions 22, 23, 24, 25, 29, 30, 36, 37, 40, 41, 45, 46 Ignore questions with ethers Page 4 of 7

Exam 5 (Thursday, August 6, 2015) Chapter 11 Carbonyl Compounds I Introduction The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives 11.1 1,2 Carboxylic Acids and Carboxylic Acid Derivatives Found in Nature 11.4 How Carboxylic Acids and Carboxylic Acids Compounds React 11.5 5 Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives 11.6 6, 7 The Reactions of Acyl Chlorides 11.7 8, 9, 10 The Reactions of Esters 11.8 11, 12, 13 Acid-Catalyzed Ester Hydrolysis 11.9 14, 15, 16, 17 Soaps, Detergents, and Micelles 11.10 18 The Reactions of Carboxylic Acids 11.11 19, 20, 21 The Reactions of Amides 11.12 22, 23 Acid-Catalyzed Amide Hydrolysis 11.13 Penicillin The Synthesis of Carboxylic Acid Derivatives 11.14 Synthetic Polymers End of the Chapter Questions 26, 27, 31, 34, 35, 36, Chapter 12 Carbonyl Compounds II Nomenclature of Aldehydes and Ketones 12.1 2,3 How Aldehydes and Ketones React 12.3 Grignard Reagents 12.4 5 Reactions of Carbonyl Compounds with Grignard Reagents 12.5 6,,7, 8, 9 Reactions of Carbonyl Compounds with Hydride Ions 12.6 11 Reactions of Aldehydes and Ketones with Amines 12.7 13a, c, d (primary amines only) Reactions of Aldehydes and Ketones with Water 12.8 14 Reactions of Aldehydes and Ketones with Alcohols 12.9 16, 17 Nucleophilic Addition to α,β -unsaturated Carbonyl Compounds 12.10 End of the Chapter Questions 19, 20, 31, 33, 34bd, 36, 37, 40, Chapter 13 Carbonyl Compounds III Introduction The Acidity of an -Hydrogen 13.1 1, 2, 3, 5 Keto-Enol Tautomers 13.2 Keto-Enol Interconversion 13.3 6, 7 Page 5 of 7

Alkylation of Enolate Ions 13.4 8, 9 Aldol Addition 13.5 10 Dehydration of the Product of an Aldol Addition 13.6 12, 13 Claisen Condensation Forms a β-keto Ester 13.7 14, 15 Caraboxylic Acids with a Car only Group at the 3- Position can be Decarboxylated 13.8 17 Reactions at the α Carbon in Biological Systems 13.11 21, 22 End of the Chapter Questions 25,28, 32, 34, 44 Page 6 of 7

On this page, If time permits. Check the in-class announcements. Chapter 15 The Organic Chemistry of Carbohydrates The Classification of Carbohydrates 15.1 1 The D- and L- Notation 15.2 2 (given the structure of the D-isomer) The Configuration of Aldoses 15.3 3 The Configuration of Ketoses 15.4 4 Measuring the Blood Glucose Levels of Diabetics Monosaccharides form Cyclic Hemiacetals 15.9 13 Glucose is the Most Stable Aldohexose 15.10 14 The Formation of Glycosides 15.11 Reducing and Nonreducing Sugars 15.12 15 Disaccharides 15.13 Polysaccharides 15.14 16 Heparin, Vitamin C, Controlling Fleas Carbohydrates on Cell Surfaces 15.16 17 Synthetic Sweeteners 15.17 End of the Chapter Questions 19, 25, 28, 29, 33 Chapter 16 The Organic Chemistry of Amino Acids, Peptides, and Proteins The Classification and Nomenclature of Amino Acids 16.1 The Configuration of Amino Acids 16.2 1 The Separation of Amino Acids 16.5 11 Peptide Bonds and Disulfide Bonds 16.6 12, 13, 14, 15, 16 The Strategy of Peptide Bond Synthesis: N- Protection and C-Activation 16.7 17 Determining the Primary Structure of a Peptide or Protein 16.9 End of the Chapter Questions 29, 31ad, Page 7 of 7